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    Dutchess County, NY Short Term Rental Properties for Sale

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    6 properties
    Duplex Property With Outbuildings
    Updated: Apr 22
    Duplex Property With Outbuildings

    32 Old Route 199, Red Hook, NY 12571

    $849,000
    3,500 sqft 4.00 AC lot
    3,500‑square‑foot duplex property on 4 acres
    Two residences with a 4‑bedroom, 3‑bathroom unit and a 2‑bedroom, 2‑bathroom unit
    Finished basement included with the larger unit
    Wood‑burning fireplace and additional wood stove in both residences
    Cottage, former sheep barn, chicken coops, and former organic garden area
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    Duplex Property with Guest Cottage
    Updated: Apr 20
    Duplex Property with Guest Cottage

    32 Old Route 199, Red Hook, NY 12571

    $849,000
    4.00 AC lot
    4‑acre property with two separate living units
    Unit One includes 4 bedrooms, 3 bathrooms, and a finished lower level
    Unit Two offers 2 bedrooms and 2 bathrooms with a short‑term rental history
    Studio cottage, former sheep barn with storage, chicken coops, and garden areas
    Wood‑burning fireplaces in both units plus a wood stove
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    Lakefront Land With Private Island
    Lakefront Land With Private Island

    71 Lake Shore Road, Pine Plains, NY 12567

    $975,000
    0.85 AC lot

    Three-parcel offering with a barn, floating dock, and an equipped island glamping setup.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    32 Old Route 199, Red Hook, NY 12571

    $849,000
    4.00 AC lot

    Two spacious living units on four acres, with wood burning fireplaces, wood stove, and pastoral outdoor living spaces.

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    Remodeled Short-Term Rental Property
    Remodeled Short-Term Rental Property

    4523 Route 199, Millerton, NY 12546

    $649,000

    Main residence with a separate two-bedroom cottage and multiple documented accommodation configurations.

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    Turn-Key Estate with Rental History
    Turn-Key Estate with Rental History

    18 Stagecoach Ln, Amenia, NY 12501

    $2,300,000

    Georgian estate with cottages, renovated for vacation rentals.

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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 6 Active listings in Dutchess County, NY, we suggest exploring several alternatives:

    Dutchess County, NY Short Term Rental Properties Market Trends and Statistics

    Explore 6 short term rental properties for sale in Dutchess County, NY, showcased through 6 active listings on our real estate platform. These investment opportunities span a total of 3,500 square feet of properties for sale, with an estimated market value of $6,471,000.

    Sale prices for short term rental properties in Dutchess County, NY start at $649,000, averaging $1,078,500, and reaching up to $2,300,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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